Thionyl Chloride → Methyl 4-hydroxy-3,5-dimethylbenzoate

HRID 1641993Notes

Reaction equation

HRID 1641993 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[C:17](=O)(O)[O-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1383874-Hydroxy-3,5-dimethylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 12389264Methyl 4-hydroxy-3,5-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,5-dimethyl-4-hydroxybenzoic acid (2 g, 0.012 mol) in anhydrous methanol (60 mL) was cooled in an ice-bath and thionyl chloride (5 mL) was added drop wise to this solution. The reaction was stirred in the ice-bath for one hour and was then warmed to room temperature and stirred for 16 hours. Solid sodium bicarbonate was then added to neutralize the acid and then the mixture was evaporated to dryness by rotary evaporation. The residue was partitioned between ethyl acetate and water (100 mL each). The ethyl acetate layer was separated and washed once with brine. It was then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. Yield=2.146 g, white powder.

Workup

  1. customthe mixture was evaporated to dryness by rotary evaporation
  2. customThe residue was partitioned between ethyl acetate and water (100 mL each)
  3. customThe ethyl acetate layer was separated
  4. washwashed once with brine
  5. dry with materialIt was then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-24ddfd9b89464e87a3b59a907be35bfb
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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